JP2014502376A - キラル液晶ポリマーのカラーシフト特性の簡易制御 - Google Patents
キラル液晶ポリマーのカラーシフト特性の簡易制御 Download PDFInfo
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- JP2014502376A JP2014502376A JP2013542507A JP2013542507A JP2014502376A JP 2014502376 A JP2014502376 A JP 2014502376A JP 2013542507 A JP2013542507 A JP 2013542507A JP 2013542507 A JP2013542507 A JP 2013542507A JP 2014502376 A JP2014502376 A JP 2014502376A
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- precursor composition
- liquid crystal
- salt
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- acryloyloxy
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- 229920000106 Liquid crystal polymer Polymers 0.000 title description 11
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 title description 11
- 239000000203 mixture Substances 0.000 claims abstract description 209
- 239000002243 precursor Substances 0.000 claims abstract description 143
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 103
- 150000003839 salts Chemical class 0.000 claims abstract description 78
- 230000008859 change Effects 0.000 claims abstract description 5
- -1 lithium tetrafluoroborate Chemical compound 0.000 claims description 114
- 150000001875 compounds Chemical class 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 50
- 239000002019 doping agent Substances 0.000 claims description 39
- 239000000758 substrate Substances 0.000 claims description 37
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- 238000010438 heat treatment Methods 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 14
- 238000007639 printing Methods 0.000 claims description 13
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- 238000004806 packaging method and process Methods 0.000 claims description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 7
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- 235000013361 beverage Nutrition 0.000 claims description 6
- 235000015872 dietary supplement Nutrition 0.000 claims description 6
- IIPYXGDZVMZOAP-UHFFFAOYSA-N lithium nitrate Chemical compound [Li+].[O-][N+]([O-])=O IIPYXGDZVMZOAP-UHFFFAOYSA-N 0.000 claims description 6
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 150000003863 ammonium salts Chemical class 0.000 claims description 5
- 235000013305 food Nutrition 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- 239000011159 matrix material Substances 0.000 claims description 5
- 239000003505 polymerization initiator Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 238000012546 transfer Methods 0.000 claims description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
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- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 4
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- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical group [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 claims description 3
- 229910001486 lithium perchlorate Inorganic materials 0.000 claims description 3
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 239000004317 sodium nitrate Substances 0.000 claims description 3
- 235000010344 sodium nitrate Nutrition 0.000 claims description 3
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 claims description 3
- 238000007766 curtain coating Methods 0.000 claims description 2
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- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
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- HQABUPZFAYXKJW-UHFFFAOYSA-O butylazanium Chemical compound CCCC[NH3+] HQABUPZFAYXKJW-UHFFFAOYSA-O 0.000 claims 1
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
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- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 3
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
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- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 3
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 241001122767 Theaceae Species 0.000 description 2
- NLGINBDFXRCWQW-UHFFFAOYSA-N [3-methyl-4-[4-(4-prop-2-enoyloxybutoxy)benzoyl]oxyphenyl] 4-(4-prop-2-enoyloxybutoxy)benzoate Chemical compound C=1C=C(OC(=O)C=2C=CC(OCCCCOC(=O)C=C)=CC=2)C(C)=CC=1OC(=O)C1=CC=C(OCCCCOC(=O)C=C)C=C1 NLGINBDFXRCWQW-UHFFFAOYSA-N 0.000 description 2
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- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
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- KLDXJTOLSGUMSJ-KVTDHHQDSA-N (3r,3ar,6r,6ar)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical class O[C@@H]1CO[C@@H]2[C@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-KVTDHHQDSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
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- 125000003562 2,2-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- QMIZKXJRSSJRSH-UHFFFAOYSA-N 2-[4-[2-carboxy-5-(4-prop-2-enoyloxybutoxycarbonyloxy)phenyl]-3-methylphenyl]-4-(4-prop-2-enoyloxybutoxycarbonyloxy)benzoic acid Chemical compound CC1=CC(C=2C(=CC=C(OC(=O)OCCCCOC(=O)C=C)C=2)C(O)=O)=CC=C1C1=CC(OC(=O)OCCCCOC(=O)C=C)=CC=C1C(O)=O QMIZKXJRSSJRSH-UHFFFAOYSA-N 0.000 description 1
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- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
- C09K19/586—Optically active dopants; chiral dopants
- C09K19/588—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
- Liquid Crystal (AREA)
- Polarising Elements (AREA)
- Credit Cards Or The Like (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42058210P | 2010-12-07 | 2010-12-07 | |
| EP2010069051 | 2010-12-07 | ||
| EPPCT/EP2010/069051 | 2010-12-07 | ||
| US61/420,582 | 2010-12-07 | ||
| PCT/EP2011/071935 WO2012076533A1 (en) | 2010-12-07 | 2011-12-06 | Simplified control of color shifting properties of a chiral liquid crystal polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014502376A true JP2014502376A (ja) | 2014-01-30 |
| JP2014502376A5 JP2014502376A5 (enExample) | 2014-12-25 |
Family
ID=45440493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013542507A Pending JP2014502376A (ja) | 2010-12-07 | 2011-12-06 | キラル液晶ポリマーのカラーシフト特性の簡易制御 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8951438B2 (enExample) |
| JP (1) | JP2014502376A (enExample) |
| KR (1) | KR20140004081A (enExample) |
| CN (1) | CN103314076B (enExample) |
| AR (1) | AR084181A1 (enExample) |
| AU (1) | AU2011340610A1 (enExample) |
| BR (1) | BR112013013792A2 (enExample) |
| CA (1) | CA2818021A1 (enExample) |
| CO (1) | CO6731091A2 (enExample) |
| EA (1) | EA201390729A1 (enExample) |
| IL (1) | IL226019A0 (enExample) |
| MA (1) | MA34718B1 (enExample) |
| MX (1) | MX2013005926A (enExample) |
| MY (1) | MY160515A (enExample) |
| PH (1) | PH12013501133A1 (enExample) |
| SG (1) | SG190966A1 (enExample) |
| TW (1) | TWI506126B (enExample) |
| UY (1) | UY33770A (enExample) |
| WO (1) | WO2012076533A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019188846A1 (ja) * | 2018-03-29 | 2019-10-03 | 富士フイルム株式会社 | 画像形成方法 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150096750A (ko) | 2012-12-20 | 2015-08-25 | 시크파 홀딩 에스에이 | 무작위 분포된 크레이터를 안에 포함하는 키랄 액정 중합체 층 또는 패턴 |
| TW201502257A (zh) | 2013-07-10 | 2015-01-16 | Sicpa Holding Sa | 包括可印碼與手性液晶聚合物層的標記 |
| US10654307B2 (en) | 2013-10-17 | 2020-05-19 | Sicpa Holding Sa | Rotogravure printing processes for producing optically variable security features |
| TW201520216A (zh) | 2013-10-21 | 2015-06-01 | Sicpa Holding Sa | 對掌性摻雜物與使用聚合性液晶材料標記之識別法及鑑別法 |
| CN105899642B (zh) * | 2013-11-08 | 2021-12-14 | 锡克拜控股有限公司 | 基于手性液晶前体和改性树脂的复合标记 |
| US10308872B2 (en) | 2013-11-08 | 2019-06-04 | Sicpa Holding Sa | Composite marking based on chiral liquid crystal precursors and modifying resins |
| ES2726851T3 (es) | 2013-11-08 | 2019-10-09 | Sicpa Holding Sa | Marca compuesta sin sal basada en precursores de cristales líquidos quirales que comprenden dopantes de acrilato quirales |
| TW201601928A (zh) | 2014-03-31 | 2016-01-16 | 西克帕控股有限公司 | 包含對掌性液晶聚合物與發光物質的標記 |
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2011
- 2011-12-06 UY UY0001033770A patent/UY33770A/es not_active Application Discontinuation
- 2011-12-06 EA EA201390729A patent/EA201390729A1/ru unknown
- 2011-12-06 CA CA2818021A patent/CA2818021A1/en not_active Abandoned
- 2011-12-06 KR KR1020137012703A patent/KR20140004081A/ko not_active Withdrawn
- 2011-12-06 MX MX2013005926A patent/MX2013005926A/es unknown
- 2011-12-06 JP JP2013542507A patent/JP2014502376A/ja active Pending
- 2011-12-06 BR BR112013013792A patent/BR112013013792A2/pt not_active IP Right Cessation
- 2011-12-06 AU AU2011340610A patent/AU2011340610A1/en not_active Abandoned
- 2011-12-06 SG SG2013042585A patent/SG190966A1/en unknown
- 2011-12-06 AR ARP110104567A patent/AR084181A1/es unknown
- 2011-12-06 PH PH1/2013/501133A patent/PH12013501133A1/en unknown
- 2011-12-06 MY MYPI2013002069A patent/MY160515A/en unknown
- 2011-12-06 CN CN201180058605.0A patent/CN103314076B/zh not_active Expired - Fee Related
- 2011-12-06 WO PCT/EP2011/071935 patent/WO2012076533A1/en not_active Ceased
- 2011-12-07 TW TW100144996A patent/TWI506126B/zh not_active IP Right Cessation
- 2011-12-07 US US13/313,242 patent/US8951438B2/en active Active
-
2013
- 2013-04-28 IL IL226019A patent/IL226019A0/en unknown
- 2013-06-05 MA MA35971A patent/MA34718B1/fr unknown
- 2013-06-06 CO CO13137642A patent/CO6731091A2/es unknown
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| JPH1124054A (ja) * | 1997-07-09 | 1999-01-29 | Daicel Chem Ind Ltd | コレステリック液晶表示素子 |
| JP2009042409A (ja) * | 2007-08-08 | 2009-02-26 | Mitsui Chemicals Inc | 液晶シール剤、それを用いた液晶表示パネルの製造方法及び液晶表示パネル |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019188846A1 (ja) * | 2018-03-29 | 2019-10-03 | 富士フイルム株式会社 | 画像形成方法 |
| JPWO2019188846A1 (ja) * | 2018-03-29 | 2021-04-22 | 富士フイルム株式会社 | 画像形成方法 |
| JP7087063B2 (ja) | 2018-03-29 | 2022-06-20 | 富士フイルム株式会社 | 画像形成方法 |
| US11453230B2 (en) | 2018-03-29 | 2022-09-27 | Fujifilm Corporation | Image forming method |
Also Published As
| Publication number | Publication date |
|---|---|
| UY33770A (es) | 2012-06-29 |
| TW201300514A (zh) | 2013-01-01 |
| IL226019A0 (en) | 2013-06-27 |
| PH12013501133A1 (en) | 2019-09-02 |
| BR112013013792A2 (pt) | 2016-09-13 |
| US20120141745A1 (en) | 2012-06-07 |
| TWI506126B (zh) | 2015-11-01 |
| MA34718B1 (fr) | 2013-12-03 |
| AR084181A1 (es) | 2013-04-24 |
| WO2012076533A1 (en) | 2012-06-14 |
| AU2011340610A1 (en) | 2013-05-30 |
| MY160515A (en) | 2017-03-15 |
| EA201390729A1 (ru) | 2013-09-30 |
| CO6731091A2 (es) | 2013-08-15 |
| CN103314076A (zh) | 2013-09-18 |
| SG190966A1 (en) | 2013-07-31 |
| MX2013005926A (es) | 2013-08-26 |
| US8951438B2 (en) | 2015-02-10 |
| CA2818021A1 (en) | 2012-06-14 |
| KR20140004081A (ko) | 2014-01-10 |
| CN103314076B (zh) | 2015-09-02 |
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